Like a Virgin by Madonna is featured in The Power of Madonna, the fifteenth episode of Season One. It is sung by Emma and Will, Finn and Santana, and Jesse and Rachel.

The song shows Finn, Emma, and Rachel being unsure about losing their virginity and Santana, Will, and Jesse trying to convince the other to go through with it. Rachel and Jesse are in Rachel's room, Santana and Finn are in a motel room, and Will and Emma are at Will's house. This song is a dream sequence, as Finn and Santana are later revealed to be the only ones to go through with their plans (Finn losing his virginity, but Rachel and Emma keeping theirs).